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An unfinished manifesto on fantasy managing Team Cuba to the top.

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I’ve been in a fantasy baseball keeper league for the past four years. There’s been good times (a third place finish in 2007!) and bad times (trading big-time prospects Grady Sizemore and Curtis Granderson for an aging Brian Giles during my inaugural season, 2006), but to say I’ve enjoyed playing the game is an understatement.

This year, however, has left something to be desired.

Despite having some top Major League Baseball talent, Team Cuba is wildly underperforming, sitting lazily between sixth, seventh, and eighth place.

Meanwhile, my friend Troy’s All-Web Team is soaring by everyone else, resting comfortably in first with a more than 20 point lead. If I have hopes of even breaking the top three, I need to amass nearly 20 points to simply close the gap between Team Cuba and the frontrunners. I’m playing like the Washington Nationals, but should be scoring like the Los Angeles Angels of Anaheim.

If this were a major league team, I would have received the dubious “vote of confidence” from my general manager by now.

Since the beginning of the season, I’ve made 45 moves, the third most in the league, by acquiring and dropping players through trades, the waiver wire, and free agency. Sure it seems like I’ve been active, attempting to field the best product possible. But most of the moves have been of the uncircumstantial kind, made more to make myself feel like I was doing something than to improve my positioning. I never focused on the statistics I needed, but rather on acquiring the newest, hottest piece of fantasy baseball ass I could; be it pitchers, who, since I was already leading most of the pitching categories, I didn’t need, or hitters, who would inevitably stop hitting as soon as I picked them up (as is usually the case).

The worst part is, I never flipped those fad players into anything of worth, instead just dropping them once their time was up.

After reading Sam Walker’s Fantasyland, I decided that my team’s middling aspirations were less a product of team performance than the product of shoddy management.

So I’m making moves to rocket Team Cuba to the top, or at least the top three.We gon' make it boys.

All my troubles started at the draft, which took place about one week before the beginning of the 2009 MLB season. I’d done some preparation, picking up fantasy baseball magazines, the uber-useful Baseball America Prospect Handbook, and by reading almost any online article I could get my cursor on. But I’m of the garden-variety, don’t-believe-just-the-stats, type of fantasy player; I left some of the draft up to nothing more than intuition.

That was probably a mistake.

I drafted Baltimore second baseman Brian Roberts in the second round as my first pick since I had agreed to “keep” the Met’s Johan Santana from the previous season. There were so many good players still available (Arizona’s Dan Haren, Minnesota’s Joe Mauer, Seattle’s Ichiro Suzuki among them) that picking a light-hitting, aging, second-bagger at this point was completely unwarranted. A pressure packed situation and one mouse click later and it appeared as though my season was destined for failure.

I regained my footing after that, however, making solid picks for the next six rounds. I spent the better part of the later rounds toiling in the dregs of the league though, making hasty and fruitless picks that, looking back, make me shake my head in disbelief. I was left with a team that, despite a strong core, was weak on hitting and would have to rely on aging sluggers and unproven rookies. Simply put, aside from a few bright spots, it wasn’t that good or the slightest bit reliable.

Not the best draft.

And it got worse from there.

I owned Texas’ Kevin Millwood for 12 days in late April. After giving up four earn runs in Toronto on the 23rd, I kicked him to curb. His ERA hasn’t risen above 3.50 since and he barely missed his second career All-Star appearance last week.

I also rostered Seattle’s Russell Branyan twice before releasing him for good on May 12th. He rewarded me by homering on the 13th. And then the 17th. And then the 18th. He’s now tied for second place in the American League with 21 home runs, a stat Team Cuba has been aching for since the start of the season. The bashers I drafted (the injured Met Carlos Delgado, the Royal’s Mike Jacobs, and the A’s Jason Giambi) have 25 home runs combined and a mean batting average of .238.

My shortstop, the Royal’s Mike Aviles, batted under .200 for most of April and May. Delgado went on the disabled list on May 11 and has yet to return. Jason Motte, the Cardinal’s forecasted closer, blew his first save of the year and never got the job back. For the first month, Rockie’s pseudo-ace Aaron Cook’s ERA approached 10.00. The hits just kept coming.

However, every move wasn’t bad.

Because the Dodger’s Russell Martin started off colder than a polar bear’s toe nails, I was forced to pick up Detroit’s Brandon Inge, who had homered in each of the first three games of the season. Inge spent time playing mostly everywhere in 2008, including behind the dish, so he was eligible at catcher, outfield, and third base in 2009. His versatility and the fact that he hasn’t really stopped hitting home runs, has kept Cuba’s head above water.

The only other reason Team Cuba has any offensive punch is because of Arizona’s shaggy haired slugger Mark Reynolds. Added on May 12th, Reynolds has easily been the top offensive performer on Team Cuba and since strikeouts don’t count in this league, he’s been just as valuable as any slugger out there.

After those moves, I rested on my laurels, not doing much for the next month, compiling points in the pitching categories but nowhere else.

But now I’m incensed. Fantasyland created a monster in me, driving me (possibly hopelessly) towards the goal of a top tier finish.

But gaining 20 points is no laughing matter. One league mate has already chided me, stating, “Haha, you got no chance, Dylan.”

Whatever. Ignorance is bliss.

I decided that my best course of action would be making shrewd moves. The league usually lambasts anyone who tries to make any trades of circumstance, so I decided I’d have to play under the radar, grabbing a few home runs, runs, and RBI from unheralded players.

Shrewd moves.

The phrase kept going through my head, like an unspoken mantra. I put it into action for the first time on June 16, acquiring the Dodger’s James Loney and the Rockie’s Ian Stewart for Baltimore’s Brian Roberts. I sent out a few points in forecasted steals and runs, but received a huge boost in home runs and RBI. The best part is that my end of the deal has started to run a little bit this year, making the sting a little less painful.

And then I sent beguiled Texas slugger Chris Davis to another team for an equally ailing Magglio Ordonez. The deal turned out to be a wash, seeing as how Davis is now toiling in Triple-A and Ordonez is part of a platoon in Detroit’s outfield. But still, the move was part of my plan: little risk with the chance for a great return.

After realizing that I’d been holding steady in the top of the pitching categories, I thought it would be a great time to make waves and deal one of my aces. The Royal’s Zack Greinke is having a career year, but there’s no way he can possibly keep his current pace. Every start he’s making these days, his ERA is going up, and while it’s still at a paltry 2.00, it should regress sooner rather than later. Plus, even with him dealt, I’d still have a formidable rotation helmed by the Met’s Johan Santana and the Brewer’s Yovani Gallardo.

I needed offense. I needed the best offensive player in the league (other than Albert Pujols). I needed the Red Sox’s Jason Bay.

Bay has been a beast in the American League East for the past two years. His swing was built for Fenway Park, where he routinely cracks doubles and home runs into and over the Green Monster. He plays in the league’s most potent offense, punctuated by a revived David Ortiz and the on-base machine that is Kevin Youkilis and Dustin Pedroia. Even if he’s not swinging particularly well, there’s still incredible incentive to bring him in: he’ll drive in runs even on a bad day.

Greinke’s departure was bittersweet. I’d seen him grow into an All-Star, a Cy Young-caliber hurler you’d want to start a team around. But that’s the hardest part about fantasy baseball: you get attached to players for nostalgia’s sake and oftentimes it can bite you in the ass.

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